Plan ahead if possible and go off the player's signing schedule.
They usually release the schedule a week or so before SoxFest.
You like can only get one item signed by the player per day and each
player has max # of autographs (I think 250, 300 max...)

Friday is best day if you have the hotel pass for autographs.
Try to get the main guys you want that day.

Sat probably the worse day for autographs. It's the busiest day.

Sun is OK but alot of the main players may not be there for Sun.

Stuff for sale. They have usually same stuff from the garage and clubhouse sale there. Some vendors too.

Also even though the event opens at say 9:00am people tend to line up as early as 6:00am. And some never go to sleep, just wait in line all night. This assures they can get the player that they want. The system is a wrist band system whereas first come first to get a wrist band. After the limit has been given out (250-300) the autograph limit is reached and the line is closed. Wrist bands are given out maybe 1 1/2 to 2 hours prior to the signing time and only one wrist band is allowed on a person. So say Thomas is signing @ 9 and Ventura is signing @ 10:30 you have to wait until you get Thomas and then get over to Ventura in hopes all the wrist bands are still being handed out. If I can help you out with any other questions let me know.

Depends on what you value. I like the seminars/town halls and the vendor area. I also like having a beer at the hotel bar and seeing players and coaches doing the same. I don't care about autographs. So the last few years it has become not worth it to me because the vendor area has decreased, players havent been mingling after hours as much, and the admission price has increased.